[C:1]([C:3]1[C:13]2[CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:22][OH:23].C(=O)(O)[O-].[Na+]>C(O)C>[OH:23][NH:22][C:1](=[NH:2])[C:3]1[C:13]2[CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=11,1-dimethylethyl 6-cyano-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 14) (1.15 g), hydroxylamine hydrochloride (1.18 g) and sodium bicarbonate (1.76 g) were heated at 60° C. in ethanol (100 ml) for 18 hours under argon. The cooled reaction was evaporated to dryness, partitioned between DCM (100 ml) and water (100 ml). The DCM layer was collected and the water layer washed with DCM (50 ml). The combined DCM layers were dried and evaporated. The title compound (506 mg) was isolated by chromatography eluting with 5% methanol in DCM. δH (400 MHz, CDCl3) 7.27 (1H, s) 7.16-7.13 (2H, m), 5.38 (1H, br. s), 3.58-3.55 (4H, m), 3.05 (2H, br. s), 2.89 (2H, br. s) 1.46 (2H br. s), 1.12 (9H, br. s); MS (ES) C16H23N3O3 requires 305; found 306 [M+H]+.
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